| | N-Methylaniline Basic information |
| | N-Methylaniline Chemical Properties |
| Melting point | -57 °C (lit.) | | Boiling point | 196 °C (lit.) | | density | 0.989 g/mL at 25 °C (lit.) | | vapor pressure | 0.5 hPa (20 °C) | | refractive index | n20/D 1.571(lit.) | | Fp | 174 °F | | storage temp. | Store below +30°C. | | solubility | water: slightly soluble30g/L | | form | Liquid | | pka | 4.84(at 25℃) | | color | Clear yellow to brown | | Odor | Moderate aniline-type. | | PH | 7.6 (1g/l, H2O, 20℃) | | Water Solubility | 30 g/L | | Sensitive | Air Sensitive | | Merck | 14,6019 | | BRN | 741982 | | Henry's Law Constant | (x 10-5 atm?m3/mol):
1.19 at 25 °C (approximate - calculated from water solubility and vapor pressure) | | Exposure limits | NIOSH REL: TWA 0.5 ppm (2 mg/m3), IDLH 100 ppm; OSHA PEL: TWA 2
ppm (9 mg/m3); ACGIH TLV: TWA 0.5 ppm (adopted). | | Stability: | Incompatible with strong oxidizing agents. Discolours upon exposure to air. | | InChIKey | AFBPFSWMIHJQDM-UHFFFAOYSA-N | | LogP | 1.66 at 20℃ | | CAS DataBase Reference | 100-61-8(CAS DataBase Reference) | | NIST Chemistry Reference | Aniline, N-methyl-(100-61-8) | | EPA Substance Registry System | N-Methylaniline (100-61-8) |
| Hazard Codes | T,N | | Risk Statements | 23/24/25-33-50/53 | | Safety Statements | 28-36/37-45-60-61-28A | | RIDADR | UN 2294 6.1/PG 3 | | WGK Germany | 3 | | RTECS | BY4550000 | | F | 8 | | Autoignition Temperature | 500 °C | | TSCA | Yes | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29214200 | | Hazardous Substances Data | 100-61-8(Hazardous Substances Data) | | Toxicity | LD in rabbits (g/kg): 0.28 orally; in rabbits, cats (mg/kg): 24, 24 i.v. (Treon) | | IDLA | 100 ppm |
| | N-Methylaniline Usage And Synthesis |
| Chemical Properties | N-Methylaniline is a yellow to light brown oily liquid with a weak, ammonia-like odor. soluble in ethanol, ether, chloroform, slightly soluble in water. Turns reddishbrown if left standing. | | Physical properties | Colorless to yellow to pale brown liquid with a faint, ammonia-like odor. Odor threshold
concentration is 1.7 ppm (quoted, Amoore and Hautala, 1983). | | Uses | N-Methylaniline is used as a solvent and in organic synthesis. It is used in the production of cationic brilliant red FG, cationic pink B, reactive yellow brown KGR, etc. in the dye industry. N-methylaniline is an intermediate in the synthesis of the insecticide buprofezin and the herbicide mefenacet. | | Uses | N-methylaniline was used as raw material, and metal-organic skeleton material CAU-10pydc was used as catalyst to catalyze the reaction of CO2 with n-methylaniline to produce N-methyl-N-phenylformamide in mild conditions and green solvent acetonitrile[1]. Poly (N-methylaniline) (PNMA) was prepared by the electrooxidation of N-methylaniline in acidic aqueous solution. PNMA prepared in acidic aqueous solution with different organic solvents and anions had different conductivity. Such as the experimental group added acetonitrile, N, N-dimethylformamide and dimethylsulfoxide, and the experimental group which adding dimethylsulfoxide had the strongest conductivity[2].
References:
[1] Zhiqiang Wang, Chenghua Deng, Xiao Liu, Wenmin Wang, Highly efficient conversion of CO2 into N-formamides catalyzed by a noble-metal-free aluminum-based MOF under mild conditions, 2023, 52, 11163-11167.
[2] Jun YANO , Hiroko YOSHIKAWA , Tomomi MUKAI , Sumio YAMASAKI , Akira KITANI, Effect of Anions and Added Organic Solvents of Polymerizing Solutions on the Conductivity of Poly (N-methylaniline), 2006, 74, 42-48. | | Preparation | N-methylaniline was synthesized by the reaction of aniline with dimethyl sulfate. Dimethyl sulfate was added dropwise to the mixed solution of aniline and water below 10°C, stirred for 1 h, and then added dropwise with 30% sodium hydroxide solution. The upper layer is the organic phase, and the lower layer is extracted with benzene. After the benzene is recovered from the extract, the obtained oil Chemicalbook-like substance is combined with the organic phase to obtain a mixture of aniline, N-methylaniline and N,N-dimethylaniline. The mixture was treated with sulfuric acid, and the aniline formed sulfate crystals which were filtered off. N,N-dimethylaniline can be converted to N-methylaniline by the following reaction. | | Application | N-Methylaniline (NMA) was used in the preparation of self-assembled poly(N-methylaniline)-lignosulfonate (PNMA-LS) composite spheres with reactive silver-ion adsorbability. NMA was also used in electrodeposition of poly(N-methylaniline) (PNMA) coatings on a steel disc electrode using potentiodynamic, potentiostatic and galvanostatic techniques. | | Definition | ChEBI: N-methylaniline is a methylaniline that is aniline carrying a methyl substituent at the nitrogen atom. It is a phenylalkylamine, a secondary amine and a methylaniline. It derives from an aniline. | | Synthesis Reference(s) | Chemical and Pharmaceutical Bulletin, 14, p. 1007, 1966 DOI: 10.1248/cpb.14.1007
Journal of the American Chemical Society, 107, p. 493, 1985 DOI: 10.1021/ja00288a037
Synthetic Communications, 13, p. 601, 1983 DOI: 10.1080/00397918308059535 | | General Description | Chemical oxidation of N-methylaniline with dichromate (oxidant) has been studied by Raman spectroscopy. | | Hazard | Toxic by ingestion, inhalation, and skin
absorption. Methemoglobinemia and central nervous system impairment. | | Health Hazard | Recommended Personal Protective Equipment: Approved respirator; rubber gloves; splash proof goggles; Symptoms Following Exposure: Inhalation causes dizziness and headache. Ingestion causes bluish discoloration (cyanosis) of lips, ear lobes, and fingernail beds. Liquid irritates eyes. Absorption through skin produces same symptoms as for ingestion; General Treatment for Exposure: INHALATION: remove victim to fresh air and call a physician at once; administer oxygen until physician arrives. INGESTION: give large amount of water; get medical attention at once. EYES or SKIN: flush with plenty of water for at least 15 min.; if cyanosis is present, shower with soap and warm water, with special attention to scalp and finger nails; remove any contaminated clothing; Toxicity by Inhalation (Threshold Limit Value): Data not available; Short-Term Inhalation Limits: Data not available; Toxicity by Ingestion: Data not available; Late Toxicity: Data not available; Vapor (Gas) Irritant Characteristics: Data not available; Liquid or Solid Irritant Characteristics: Data not available; Odor Threshold: Data not available. | | Chemical Reactivity | Reactivity with Water No reaction; Reactivity with Common Materials: May attack some forms of plastic; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | | Safety Profile | Poison by ingestion and
intravenous routes. Moderately toxic by subcutaneous route. When heated to
decomposition it emits toxic fumes of NOx. | | Potential Exposure | The material is used as an intermediate
in organic synthesis, as a solvent and as an acid acceptor | | Carcinogenicity | N-methyl aniline (1.95 g/kg of food) given
together with sodium nitrite (1.0 g/l of drinking
water) to Swiss mice resulted in a 17% incidence
of lung adenomas and a 14% incidence
of malignant lymphomas; there were no carcinogenic
effects in animals treated with Nmethyl
aniline alone, suggesting that in vivo
nitrosation is necessary for forming carcinogenic
nitrosamines.
In bacterial mutagenicity assays N-methyl
aniline was negative with or without metabolic
activation. | | Environmental fate | Soil. Reacts slowly with humic acids or humates forming quinoidal structures (Parris, 1980). | | Shipping | UN2294 N-Methylaniline, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials. | | Purification Methods | Dry it with KOH pellets and fractionally distil it under vacuum. Acetylate, and the acetyl derivative is recrystallised to constant melting point (m 101-102o), then hydrolysed with aqueous HCl and distilled from zinc dust under reduced pressure. [Hammond & Parks J Am Chem Soc 77 340 1955, Beilstein 12 IV 241.] | | Waste Disposal | Controlled incineration
whereby oxides of nitrogen are removed from the effluent
gas by scrubber, catalytic or thermal device. |
| | N-Methylaniline Preparation Products And Raw materials |
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